HCID 12096046, compound → HCID 18761297, compound

HRID 432736Notes

Reaction equation

HRID 432736 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][CH3:25])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1>FC(F)(F)C(O)=O.O.O=[Pt]=O>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][CH3:25])[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1

Participants

5

Reactant 1

HCID 12096046HCID 12096046, compound

Product 1

HCID 18761297HCID 18761297, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-(2-Methoxyethyl)-1-{2-[2-(methylamino)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine (4.22 g, 12.3 mmol) was dissolved in 25 mL of trifluoroacetic acid and treated with PtO2 (0.5 g). The reaction mixture was shaken under H2 (3 Kg/cm2). After 4 d, an additional 0.5 g of PtO2 was added and hydrogenation was continued for an additional 3 d. The reaction was then filtered through Celite and concentrated under reduced pressure to give a yellow oil. The yellow oil was dissolved in 50 mL of H2O and extracted with 50 mL of CHCl3. The organic portion was removed and discarded. The aqueous portion was then made basic (pH˜12) by addition of 10% NaOH solution. This was then extracted with CHCl3 (6×50 mL) and the combined organic layers were dried over Na2SO4 and concentrated to a brown oil. The brown oil was dissolved in 100 mL of hot MeOH and treated with 1 g of activated charcoal. The hot solution was filtered through Celite and concentrated to dryness. The resulting gummy solid was concentrated several times with Et2O to give 3.19 g of 2-(2-methoxyethyl)-1-{2-[2-(methylamino)ethoxy]ethyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as an off-white powder. MS 348 (M+H)+; 1H NMR (300 MHz, CDCl3) δ4.84 (s, 2 H); 4.48 (t, J=5.7 Hz, 2 H); 3.84 (t, J=6.7 Hz, 2 H); 3.70 (t, J=5.7 Hz, 2 H); 3.46 (t, J=5.1 Hz, 2 H); 3.36 (s, 3 H); 3.14 (t, J=6.7 Hz, 2 H); 2.96 (m, 2 H); 2.83 (m, 2 H); 2.65 (t, J=5.1 Hz, 2 H); 2.36 (s, 3 H); 1.85 (m, 4 H).

Workup

  1. waithydrogenation was continued for an additional 3 d
  2. filtrationThe reaction was then filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow oil
  5. extractionextracted with 50 mL of CHCl3
  6. customThe organic portion was removed
  7. additionby addition of 10% NaOH solution
  8. extractionThis was then extracted with CHCl3 (6×50 mL)
  9. dry with materialthe combined organic layers were dried over Na2SO4
  10. concentrationconcentrated to a brown oil
  11. dissolutionThe brown oil was dissolved in 100 mL of hot MeOH
  12. additiontreated with 1 g of activated charcoal
  13. filtrationThe hot solution was filtered through Celite
  14. concentrationconcentrated to dryness
  15. concentrationThe resulting gummy solid was concentrated several times with Et2O

Sources & evidence

ORD record
ord-ef4cf52aa7e643ffa8d7369eb4cee030
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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